One‐Pot Transformation of Ketoximes into Optically Active Alcohols and Amines by Sequential Action of Laccases and Ketoreductases or ω‐Transaminases

An enzymatic one‐pot process for asymmetric transformation of prochiral ketoximes into alcohols or amines was developed by sequential coupling of a laccase‐catalyzed deoximation either with a ketone reduction (ketoreductase, KRED) or bioamination (ω‐transaminase, ω‐TA) in aqueous medium. An accurate...

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Bibliographic Details
Published in:ChemCatChem 2019-02, Vol.11 (4), p.1272-1277
Main Authors: Correia Cordeiro, Raquel S., Ríos‐Lombardía, Nicolás, Morís, Francisco, Kourist, Robert, González‐Sabín, Javier
Format: Article
Language:English
Subjects:
Alcohol
alcohol dehydrogenase
Alcohols
Amines
Aqueous solutions
Castor oil
enzymatic cascade
Laccase
one-pot reaction
Optical activity
oxime
transaminase
Transaminases
Transformations
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Summary:An enzymatic one‐pot process for asymmetric transformation of prochiral ketoximes into alcohols or amines was developed by sequential coupling of a laccase‐catalyzed deoximation either with a ketone reduction (ketoreductase, KRED) or bioamination (ω‐transaminase, ω‐TA) in aqueous medium. An accurate selection of biocatalysts provided the corresponding products in excellent enantiomeric excesses and overall conversions ranging from 83 to >99 % for alcohols and 70 to >99 % for amines. Likewise, the employment of exclusively 1 % (w/w) of Cremophor®, a polyethoxylated castor oil, as co‐solvent enabled to reach concentrations up to 100 mM in the chiral alcohols cascade. Choose your path: A sequential combination of laccases and either ketoreductases or ω‐transaminases proved to be an optimal method for converting ketoximes into enantiopure alcohols or amines, respectively.
ISSN:1867-3880
1867-3899
DOI:10.1002/cctc.201801900